5-[4-[3-氯-4-(3-氟苯氧基)苯胺基]-6-喹唑啉基]呋喃-2-甲醛合成路线 （共 28 条）
反应条件
1.1: ammonium acetate / Inert atmosphere 1.2: 95 °C / 750.08 - 2250.23 Torr / Inert atmosphere 2.1: triethylamine; trichlorophosphate / toluene / 2 h / Heating; Inert atmosphere 3.1: 1 h / Heating; Inert atmosphere 4.1: PdCl2(PPh3)2; sodium carbonate / ethylene glycol dimethyl ether; ethanol; water / 60 °C / Inert atmosphere View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 53, # 24 p. 8546 - 8555
反应条件
1.1: n-butyllithium / hexane; ethylene glycol dimethyl ether / 5 h / -50 °C / |Inert atmosphere 1.2: 6.5 h / -40 - 20 °C / |Inert atmosphere 2.1: palladium 10 on activated carbon; N-ethyl-N,N-diisopropylamine / methanol / 8 h / |Reflux View Scheme
反应条件
1: 2-(methanesulphonyl)ethylamine hydrochloride; 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde With acetic acid; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; N,N-dimethyl-formamide T=35°C; 1 h; 2: With sodium tris(acetoxy)borohydride in tetrahydrofuran; N,N-dimethyl-formamide T=20 - 25°C; 2 h; 3: toluene-4-sulfonic acid
参考文献
WO2010/17387 A2, ;
Page/Page column 29-30 ;
反应条件
1: 1-(methylsulfonyl)eth-2-ylamine; 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde in methanol; dichloromethane T=20°C; 2: With hydrogen in methanol; dichloromethane Inert atmosphere; 3: toluene-4-sulfonic acid in methanol; dichloromethane
参考文献
WO2012/83440 A1, ;
Page/Page column 13-14 ;
反应条件
1: triethylamine / methanol / 12 h / Reflux 2: methanol / tetrahydrofuran / 0 - 15 °C 3: methanol / 3 h / Reflux View Scheme
反应条件
1: in methanol; dichloromethane T=20°C; 2: With hydrogen in methanol; dichloromethane Inert atmosphere;
参考文献
APOTEX PHARMACHEM INC; RAHEEM, Mohommed Abdul; WEERATUNGA, Gamini; ZETINA-ROCHA, Carlos; CAMMISA, Eduardo Gustavo
Patent: WO2012/83440 A1, 2012 ;
Location in patent: Page/Page column 14 ;
反应条件
1: With acetic acid; N-ethyl-N,N-diisopropylamine in tetrahydrofuran T=40°C; 1 h; 2: With sodium tris(acetoxy)borohydride in tetrahydrofuran T=20°C; 3 h;
参考文献
ZENTIVA, K.S.; RADL, Stanislav; STEFKO, Martin; CERNY, Josef
Patent: WO2014/59956 A1, 2014 ;
Location in patent: Page/Page column 12 ;
反应条件
1: triethylamine / methanol / 12 h / Reflux 2: methanol / tetrahydrofuran / 0 - 15 °C View Scheme
参考文献
Natco Pharma Limited
Patent: US2011/263852 A1, 2011 ;
